Compound comprising a five-membered hetero ring, an organic electrical element using same and a terminal thereof

ABSTRACT

A compound having a five-membered hetero ring, an organic electrical element using the same and a terminal thereof. An organic electric element includes a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode. The organic material layer includes the compound. When the organic electric element includes the compound in an organic material layer, luminous efficiency, stability, and life span can be improved.

CROSS REFERENCE TO RELATED APPLICATIONS AND CLAIM OF PRIORITY

The present application is a continuation-in-part application to U.S.patent application Ser. No. 13/699,040, filed Nov. 20, 2012, which is aNational Phase application under U.S.C. §371 of InternationalApplication No. PCT/KR2011/003862, filed May 26, 2011, which claimspriority to Korean Patent Application No. 10-2010-0049325 filed May 26,2010, entire contents of which are incorporated herein by reference.

BACKGROUND

1. Technical Field

The present invention relates to a compound including a five-memberedhetero ring, an organic electrical element using the same, and aterminal including the organic electrical element.

2. Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy by means of anorganic material. An organic electrical element utilizing the organiclight emitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. Here, inmany cases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electrical element,and for example, may include a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, an electroninjection layer, and the like.

A material used as an organic material layer in an organic electricalelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function. Further, thelight emitting material may be divided into a high molecular weight typeand a low molecular weight type according to its molecular weight, andmay also be divided into a fluorescent material derived from electronicexcited singlet states and a phosphorescent material derived fromelectronic excited triplet states according to its light emittingmechanism. Further, the light emitting material may be divided intoblue, green, and red light emitting materials, and yellow and orangelight emitting materials required for better natural color reproductionaccording to its light emitting color.

Meanwhile, when only one material is used as a light emitting material,there occur problems of shift of a maximum luminescence wavelength to alonger wavelength due to intermolecular interactions and lowering of theefficiency of a corresponding element due to a deterioration in colorpurity or a reduction in luminous efficiency. On account of this, ahost/dopant system may be used as the light emitting material in orderto enhance the color purity and increase the luminous efficiency throughenergy transfer. This is based on the principle that if a small amountof dopant having a smaller energy band gap than a host forming a lightemitting layer is mixed in the light emitting layer, then excitonsgenerated in the light emitting layer are transported to the dopant,thus emitting light with high efficiency. With regard to this, since thewavelength of the host is shifted to the wavelength band of the dopant,light having a desired wavelength can be obtained according the type ofthe dopant.

In order to allow an organic electrical element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material constituting an organic material layer in the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, or the like, by a stable and efficient material. However, sucha stable and efficient organic material layer material for an organicelectrical element has not yet been fully developed. Accordingly, thereis a continuous need to develop new materials for an organic materiallayer.

SUMMARY

In order to solve the above-mentioned problems occurring in the priorart, embodiments of the present invention have led to the discovery of acompound including a five-membered hetero ring. Further, it was foundthat when this compound is employed in an organic electrical element,the element can be significantly improved in luminous efficiency,stability, and life span.

Accordingly, an aspect of the present invention is to provide a compoundincluding a five-membered hetero ring, an organic electrical elementusing the same, and a terminal including the organic electrical element.

In accordance with an aspect of the present invention, there is provideda compound represented by Formula below.

The inventive compound including two or more five-membered hetero ringshas proved to be a material that can not only provide high efficiencyand enhance color purity, but can also improve driving voltage in anorganic electrical element. Accordingly, the present invention providesa compound including two or more five-membered hetero rings as corecomponents, an organic electrical element using the same, and a terminalincluding the organic electrical element.

The inventive compound, which is synthesized by a compound including twoor more five-membered hetero rings, is useful as a hole injectionmaterial, a hole transport material, a light emitting material, and/oran electron transport material appropriate for both fluorescent andphosphorescent elements of all colors such as red, green, blue, andwhite.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 to 6 illustrate examples of an organic light emitting diode inwhich a compound according to the present invention may be employed.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings. Indesignation of reference numerals to components in respective drawings,it should be noted that the same elements will be designated by the samereference numerals although they are shown in different drawings.Further, in the following description of the present invention, adetailed description of known functions and configurations incorporatedherein will be omitted when it may make the subject matter of thepresent invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

An aspect of the present invention provides a compound represented byFormula 1 below.

(1) R₁, R₂, R₃, R₄, R₅, and R₆ are each independently a hydrogen atom, ahalogen atom, a cyano group, an alkoxy group, a thiol group, asubstituted or unsubstituted C1 to C50 alkyl group, a substituted orunsubstituted C1 to C50 alkoxy group, a substituted or unsubstituted C1to C50 alkenyl group, a substituted or unsubstituted C5 to C60 arylenegroup, a substituted or unsubstituted C5 to C60 aryl group, asubstituted or unsubstituted C5 to C60 aryloxy group, a substituted orunsubstituted C1 to C50 alkyl group including at least one of sulfur(S), nitrogen (N), oxygen (O), phosphorous (P), and silicon (Si), asubstituted or unsubstituted C5 to C60 heteroaryl group including atleast one of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) andsilicon (Si), or a substituted or unsubstituted C5 to C60 heteroaryloxygroup including at least one of sulfur (S), nitrogen (N), oxygen (O),phosphorous (P) and silicon (Si).

(2) R₁ and R₂, R₂ and R₃, R₃ and R₄, and R₅ and R₆ each may form asubstituted or unsubstituted, saturated or unsaturated aliphatic ring ora hetero ring having N, O, or S as a hetero atom together with anadjacent group.

(3) X is at least one of sulfur (S), oxygen (O), and silicon (Si).

(4) Ar is a hydrogen atom, a substituted or unsubstituted C1 to C50alkyl group, a substituted or unsubstituted C1 to C50 alkenyl group, asubstituted or unsubstituted C5 to C60 arylene group, a substituted orunsubstituted C5 to C60 aryl group, a substituted or unsubstituted C5 toC60 aryloxy group, a substituted or unsubstituted C1 to C50 alkyl groupincluding at least one of sulfur (S), nitrogen (N), oxygen (O),phosphorous (P), and silicon (Si), a substituted or unsubstituted C5 toC60 heteroaryl group including at least one of sulfur (S), nitrogen (N),oxygen (O), phosphorous (P) and silicon (Si), or a substituted orunsubstituted C5 to C60 heteroaryloxy group including at least one ofsulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si).

(5) Y is a substituted or unsubstituted C1 to C50 alkyl group, asubstituted or unsubstituted C1 to C50 alkenyl group, a substituted orunsubstituted C5 to C60 arylene group, a substituted or unsubstituted C5to C60 aryl group, a substituted or unsubstituted C5 to C60 aryloxygroup, a substituted or unsubstituted C1 to C50 alkyl group including atleast one of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P), andsilicon (Si), a substituted or unsubstituted C5 to C60 heteroaryl groupincluding at least one of sulfur (S), nitrogen (N), oxygen (O),phosphorous (P) and silicon (Si), or a substituted or unsubstituted C5to C60 heteroaryloxy group including at least one of sulfur (S),nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si).

(6) Z is 5, NR₇R₈, OR₉, PR₁₀R₁₁ or POR₁₀R₁₁, or SiR₁₂ wherein R₇, R₈,R₉, R₁₀, R₁₁, and R₁₂ are each independently a substituted orunsubstituted C5 to C60 aryl group or a substituted or unsubstituted C5to C60 heteroaryl group including at least one of sulfur (S), nitrogen(N), oxygen (O), phosphorous (P) and silicon (Si). Preferably, when m isthe ingeger of 0, R₇ and R₈ may not bond to each other to form a ringstructure.

(7) m has an integer from 0 to 2, and n has an integer from 1 to 2.

Specific examples of a compound including five-membered hetero ringsaccording to an embodiment of the present invention, represented byFormula 1, may include compounds represented by Formulas 2 to 7 below,but the present invention is not limited thereto.

Another aspect of the present invention provides a compound representedby Formula 2 below.

Yet another aspect of the present invention provides a compoundrepresented by Formula 3 below.

Still yet another aspect of the present invention provides a compoundrepresented by Formula 4 below.

Still yet another aspect of the present invention provides a compoundrepresented by Formula 5 below.

Still yet another aspect of the present invention provides a compoundrepresented by Formula 6 below.

Still yet another aspect of the present invention provides a compoundrepresented by Formula 7 below.

Compounds represented by Formulas 2 to 7 may be further represented byFormulas 8 to 13 below, but the present invention is not limitedthereto.

Compounds represented by Formulas 1 to 5 above each may be one ofcompounds represented by Formulas 6 to 13 above, but the presentinvention is not limited thereto. With regard to this, since there are awide range of substituents for each of R₁ to R₆, X, Ar, Y, and Z ofcompounds represented by Formula 1, it is practically difficult to coverall compounds by Formulas 6 to 13. Thus, representative compounds areillustratively described, but other compounds represented by Formula 1,not presented in Formulas 6 to 13, may also form a part of thisspecification.

There are various organic electrical elements in which the five-memberedheterocyclic compounds described with reference to Formulas 1 to 13 areused as an organic material layer. Examples of organic electricalelements to which the five-membered heterocyclic compounds describedwith reference to Formulas 1 to 13 are applicable may include an organiclight emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, an organic transistor (organic TFT), and the like.

As one example of the organic electrical elements in which thefive-membered heterocyclic compounds described with reference toFormulas 1 to 13 may be employed, an organic light emitting diode (OLED)will be described below, but the present invention is not limitedthereto, and the above described five-membered heterocyclic compoundsmay be employed in various organic electrical elements.

Another embodiment of the present invention provides an organic lightemitting diode as an organic electrical element including a firstelectrode, a second electrode, and an organic material layer interposedbetween these electrodes, in which at least one of layers included inthe organic material layer contains the compounds represented byFormulas 1 to 13.

FIGS. 1 to 6 show examples of an organic light emitting diode in which acompound according to the present invention may be employed.

An organic light emitting diode according to another embodiment of thepresent invention may be manufactured by means of manufacturing methodsand materials conventional in the art in such a manner as to have astructure known in the art, except that at least one of layers includedin an organic material layer, including a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer,and an electron injection layer, is formed in such a manner as tocontain the compounds represented by Formulas 1 to 13.

The structures of the organic light emitting diode according to anotherembodiment of the present invention are shown in FIGS. 1 to 6, but thepresent invention is not limited to these structures. In the exampleshown in FIG. 1, reference numeral “101” indicates a substrate, “102”indicates an anode, “103” indicates a hole injection layer (HIL), “104”indicates a hole transport layer (HTL), “105” indicates an emittinglayer (EML), “106” indicates an electron injection layer (EIL), “107”indicates an electron transport layer (ETL), and “108” indicates acathode. Although not shown, such an organic light emitting diode mayfurther include a hole blocking layer (HBL) for blocking movement ofholes, an electron blocking layer (EBL) for blocking movement ofelectrons, and a protective layer. The protective layer may be formed asan uppermost layer for protecting an organic material layer or acathode.

With regard to this, the five-membered heterocyclic compound describedwith reference to Formulas 1 to 13 may be contained in at least one oflayers included in an organic material layer, including a hole injectionlayer, a hole transport layer, an emitting layer, and an electrontransport layer. More specifically, the five-membered heterocycliccompound described with reference to Formulas 1 to 13 may be substitutedfor at least one of a hole injection layer, a hole transport layer, anemitting layer, an electron transport layer, an electron injectionlayer, a hole blocking layer, an electron blocking layer, and aprotective layer, or may be layered together with these layers. Ofcourse, the compound may be used in not only one layer but also two ormore layers of the organic material layers.

Especially, the five-membered heterocyclic compound described withreference to Formulas 1 to 13 may be used as a hole injection material,a hole transport material, an electron injection material, an electrontransport material, a light emitting material, and a passivation(capping) material, and particularly, may be used alone as a lightemitting material, a host, or a dopant.

For example, the organic light emitting diode according to anotherembodiment of the present invention may be manufactured by depositing ametal, a conductive metal oxide, or an alloy thereof on a substrate bymeans of PVD (physical vapor deposition) such as sputtering or e-beamevaporation to form an anode, forming an organic material layerincluding a hole injection layer, a hole transport layer, an emittinglayer, an electron transport layer, and an electron injection layerthereon, and then depositing a material, which can be used as a cathode,thereon.

In addition to this method, an organic electrical element may bemanufactured by sequentially depositing a cathode material, an organicmaterial layer, and an anode material on a substrate. The organicmaterial layer may be formed in a multi-layered structure including ahole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer, and the like, butthe present invention is not limited thereto, and the organic materiallayer may be formed in a single layer structure. Further, the organicmaterial layer may be manufactured in such a manner that a smallernumber of layers are formed using various polymer materials by means ofa solvent process, for example, spin coating, dip coating, doctorblading, screen printing, inkjet printing, or thermal transfer insteadof deposition.

In the organic light emitting diode according to another embodiment ofthe present invention, the above described five-membered heterocycliccompound may be used in a soluble process such as a spin coating processor an ink jet process.

A substrate is a support for the organic light emitting diode, and asilicon wafer, a quartz or glass plate, a metal plate, a plastic film orsheet, and the like may be used as the substrate.

An anode is disposed on the substrate. This anode injects holes into ahole injection layer disposed thereon. Preferably, a material having ahigh work function is used as an anode material so that injection ofholes into an organic material layer can be smoothly achieved. Specificexamples of an anode material that may be used in the present inventionmay include: metals such as vanadium, chromium, copper, zinc, and gold,or alloys thereof; metal oxides such as zinc oxide, indium oxide, indiumtin oxide (ITO), and indium zinc oxide (IZO); a metal-oxide combinationsuch as ZnO:Al or SnO₂:Sb; and conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT),polypyrrole, and polyaniline, but the present invention is not limitedthereto.

A hole injection layer is disposed on the anode. A material for thishole injection layer is required to have a high efficiency for injectingholes from an anode and have the ability to efficiently transport theinjected holes. To this end, the material must have a low ionizationpotential, a high transparency to visible rays, and a high stability forholes.

A material suitable for use as a hole injection material is a materialinto which holes can be readily injected from an anode at a low voltage,and the HOMO (highest occupied molecular orbital) of the hole injectionmaterial preferably ranges between a work function of an anode materialand the HOMO of an adjacent organic material layer. Specific examples ofthe hole injection material may include metal porphyrine-,oligothiophene-, and arylamine-based organic materials, hexanitrilehexaazatriphenylene- and quinacridone-based organic materials, aperylene-based organic material, and anthraquinone-, polyaniline-, andpolythiophene-based conductive polymers, but the present invention isnot limited thereto.

A hole transport layer is disposed on the hole injection layer. Thishole transport layer serves to receive holes transferred from the holeinjection layer and transfer them to an organic emitting layer disposedthereon. Further, the hole transport layer has high hole mobility andhigh stability for holes and also plays a role of blocking electrons. Inaddition to these general requirements, the hole transport layerrequires heat-resistance for an element when being applied to a vehicledisplay, and thus is preferably made of a material having a glasstransition temperature (Tg) of 70° C. or more. The examples of amaterial satisfying these requirements may include NPD (also referred toas NPB), a spiro-arylamine-based compound, a perylene-arylamine-basedcompound, an azacycloheptatriene compound,bis(diphenylvinylphenyl)anthracene, a silicon-germanium oxide compound,a silicon-based arylamine compound, and the like.

An organic emitting layer is disposed on the hole transport layer. Thisorganic emitting layer refers to a layer in which holes and electronsinjected from an anode and a cathode respectively are recombined to emitlight, and is made of a material having high quantum efficiency. Amaterial suitable for use as a light emitting material is a materialthat combines holes and electrons transferred from a hole transportlayer and an electron transport layer respectively and thereby emitslight in a visible ray range. Preferably, a material having high quantumefficiency for fluorescence or phosphorescence may be used.

As a material or a compound satisfying these requirements, for greenlight emission, Alq3 may be used, and for blue light emission, Balq(8-hydroxyquinoline beryllium salt), a DPVBi(4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl) based material, a Spiromaterial, spiro-DPVBi(Spiro-4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl), LiPBO(2-(2-benzoxazoyl)-phenol lithium salt),bis(diphenylvinylphenylvinyl)benzene, an aluminum-quinoline metalcomplex, metal complexes of imidazole, thiazole, and oxazole, or thelike may be used. In order to improve blue light emission efficiency, ablue light emitting material may be doped with a small amount ofperylene and BczVBi(3,3′[(1,1′-biphenyl)-4,4′-diyldi-2,1-ethenediyl]bis(9-ethyl)-9H-carbazole;DSA(distrylamine)). For red light emission, a green light emittingmaterial doped with a small amount of DCJTB([2-(1,1-dimethylethyl)-6-[2-(2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H-benzo(ij)quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene]-propanedinitrile)may be used. When an emitting layer is formed by means of a process suchas inkjet printing, roll coating, spin coating, or the like, a polymersuch as a polyphenylenevinylene (PPV)-based polymer or poly fluorene maybe used for an organic emitting layer.

An electron transport layer is disposed on the organic emitting layer.This electron transport layer requires a material that has highefficiency for electrons injection from a cathode disposed thereon andcan efficiently transport the injected electrons. To this end, theelectron transport layer must be made of a material having high electronaffinity, high electron mobility, and high stability to electrons.Specific examples of an electron transport material satisfying theserequirements may include an Al complex of 8-hydroxyquinoline; a complexcontaining Alg_(a); an organic radical compound; and ahydroxyflavone-metal complex, but the present invention is not limitedthereto.

An electron injection layer is laminated on the electron transportlayer. The electron injection layer may be manufactured using a lowmolecular weight material containing a metal complex compound (such asBalq, Alq3, Be(bq)2, Zn(BTZ)2, Zn(phq)2, PBD, spiro-PBD, TPBI, andTf-6P), an aromatic compound having an imidazole ring, or a boroncompound. Here, the electron injection layer may be formed in athickness range of 100 Å to 300 Å.

A cathode is disposed on the electron injection layer. This cathodeserves to inject electrons. The same material as that used for the anodeis possibly used as a material for the cathode. For efficient electroninjection, a metal having a low work function is more preferably used.Especially, an appropriate metal such as tin, magnesium, indium,calcium, sodium, lithium, aluminum, silver, or an alloy thereof may beused. Further, an electrode with a double-layer structure, such aslithium fluoride and aluminum, lithium oxide and aluminum, and strontiumoxide and aluminum, may be used with a thickness of 100 μm or less.

According to used materials, the organic light emitting diode accordingto the present invention may be of a top emission type, a bottomemission type, or a dual emission type.

In addition, the present invention provides a terminal including adisplay device, which includes the above described organic electricalelement, and a control unit for driving the display device. The terminalmeans a wired/wireless communication terminal which is currently used orwill be used in the future. The inventive terminal as described abovemay be a mobile communication terminal such as a cellular phone, and mayinclude all kinds of terminals such as a PDA, an electronic dictionary,a PMP, a remote controller, a navigation unit, a game player, variouskinds of TVs, and various kinds of computers.

EXAMPLE

Hereinafter, the present invention will be described in more detailthrough Preparation Examples and Test Examples. However, the followingexamples are only for illustrative purposes and are not intended tolimit the scope of the invention.

Preparation Example

Hereinafter, Preparation Examples or Synthesis Examples of thefive-membered heterocyclic compounds presented in Formulas 8 to 13 willbe described. However, since there are a number of five-memberedheterocyclic compounds belonging to Formula 1, some of them will beselectively described by way of example. It will be apparent to thoseskilled in the art that other five-membered heterocyclic compoundsaccording to the present invention can be prepared through PreparationExamples as described below although they are not exemplified herein.

Synthesis Method

1. Synthesis Method of Compound 1-15

With reference to Reaction Scheme 1 above, preparation methods ofintermediates A to D and a preparation method of compound 1-15 will bedescribed below.

Synthesis of Intermediate A

Dibenzothiophene was dissolved in anhydrous tetrahydrofurane (THF), andthe temperature of the reactants was lowered to −78° C. n-BuLi (2.5 M inhexane) was slowly added dropwise to the reactants, and then thereactants were stirred for 1 hour at 0° C. Subsequently, the temperatureof the reactants was lowered to −78° C., and a triisopropyl boratesolution dissolved in tetrahydrofuran (THF) was added dropwise to thereactants, followed by stirring for 12 hours at room temperature. Uponcompletion of the reaction, the reaction product was added with 1N—HClaqueous solution, stirred for 30 minutes, and then extracted with ether.A small amount of water was removed from the extract by anhydrousmagnesium sulfate (MgSO₄), the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by columnchromatography, with the result that desired intermediate A was obtainedwith a yield of 71%.

Synthesis of Intermediate B

The intermediate A obtained from the above step,2,4-dibromonitrobenzene, Pd(PPh₃)₄, and potassium carbonate (K₂CO₃) weredissolved in tetrahydrofuran (THF) and a small amount of water, followedby reflux for 24 hours. Upon completion of the reaction, the reactionproduct was cooled to room temperature, extracted with dichloromethane(CH₂Cl₂), and washed with water. A small amount of water was removedfrom the extract by anhydrous magnesium sulfate (MgSO₄), the extract wassubjected to vacuum-filtration, and then the filtrated organic solventwas concentrated. The resultant product was separated by columnchromatography, with the result that desired intermediate B was obtainedwith a yield of 57%.

Synthesis of Intermediate C

The intermediate B obtained from the above step and triphenylphosphinewere dissolved in o-DCB (o-dichlorobenzene), followed by reflux for 24hours. Upon completion of the reaction, the solvent was removed usingvacuum distillation, and then the concentrated product was separated bycolumn chromatography, with the result that desired intermediate C wasobtained with a yield of 61%.

Synthesis of Intermediate D

The intermediate C obtained from the above step, iodobenzene, Pd₂(dba)₃,P(tBu)₃, and NaOtBu were dissolved in a toluene solvent, followed byreflux for 6 hours at 110° C. Upon completion of the reaction, thereaction product was subjected to vacuum filtration through Celite andsilica gel by using a hot toluene solvent. The temperature of thefiltrate was cooled to room temperature, and then the precipitatedproduct was recrystallized again using toluene and acetone, with theresult that desired intermediate D was obtained by a yield of 77%.

Synthesis of Compound 1-15

The intermediate D obtained from the above step,bis(9,9-dimethyl-9H-fluorene-2-yl)amine, Pd₂(dba)₃, P(tBu)₃, and NaOtBuwere dissolved in a toluene solvent, followed by reflux for 24 hours at110° C. Upon completion of the reaction, the reaction product wassubjected to vacuum filtration through Celite and silica gel by using ahot toluene solvent. The temperature of the filtrate was cooled to roomtemperature, and then the precipitated product was recrystallized againusing toluene and acetone, with the result that desired compound 1-15was obtained by a yield of 68%.

2. Synthesis Method of Compounds 2-10

With reference to Reaction Scheme 2 above, preparation methods ofintermediates E to G and a preparation method of compound 2-10 will bedescribed below

Synthesis Method of Intermediate E

The intermediate A obtained from the above step,2,5-dibromonitrobenzene, P_(d)(PPh₃)₄, and potassium carbonate (K₂CO₃)were dissolved in tetrahydrofuran (THF) and a small amount of water,followed by reflux for 24 hours. Upon completion of the reaction, thereaction product was cooled to room temperature, extracted withdichloromethane (CH₂Cl₂), and washed with water. A small amount of waterwas removed from the extract by anhydrous magnesium sulfate (MgSO₄), theextract was subjected to vacuum-filtration, and then the filtratedorganic solvent was concentrated. The resultant product was separated bycolumn chromatography, with the result that desired intermediate E wasobtained with a yield of 68%.

Synthesis of Intermediate F

The intermediate E obtained from the above step and triphenylphosphinewere dissolved in o-DCB (o-dichlorobenzene), followed by reflux for 24hours. Upon completion of the reaction, the solvent was removed usingvacuum distillation, and then the concentrated product was separated bycolumn chromatography, with the result that desired intermediate F wasobtained with a yield of 71%.

Synthesis of Intermediate G

The intermediate F obtained from the above step, iodobenzene, Pd₂(dba)₂,P(tBu)₃, and NaOtBu were dissolved in a toluene solvent, followed byreflux for 6 hours at 110° C. Upon completion of the reaction, thereaction product was subjected to vacuum filtration through Celite andsilica gel by using a hot toluene solvent. The temperature of thefiltrate was cooled to room temperature, and then the precipitatedproduct was recrystallized again using toluene and acetone, with theresult that desired intermediate G was obtained by a yield of 80%.

Synthesis of Compound 2-10

The intermediate G obtained from the above step, diphenyl-4-ylamine,Pd₂(dba)₃, P(tBu)₃, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 24 hours at 110° C. Upon completion of thereaction, the reaction product was subjected to vacuum filtrationthrough Celite and silica gel by using a hot toluene solvent. Thetemperature of the filtrate was cooled to room temperature, and then theprecipitated product was recrystallized again using toluene and acetone,with the result that desired compound 2-10 was obtained by a yield of72%.

3. Synthesis Method of Compound 3-14

With reference to Reaction Scheme 3 above, preparation methods ofintermediates H and I and a preparation method of compound 3-14 will bedescribed below.

Synthesis of Intermediate H

The intermediate D obtained from the above step was dissolved inanhydrous tetrahydrofurane (THF), and the temperature of the reactantswas lowered to −78° C. n-BuLi (2.5 M in hexane) was slowly addeddropwise to the reactants, and then the reactants were stirred for 1hour at 0° C. Subsequently, the temperature of the reactants was loweredto −78° C., and a triisopropyl borate solution dissolved intetrahydrofuran (THF) was added dropwise to the reactants, followed bystirring for 12 hours at room temperature. Upon completion of thereaction, the reaction product was added with 1N—HCl aqueous solution,stirred for 30 minutes, and then extracted with ether. A small amount ofwater was removed from the extract by anhydrous magnesium sulfate(MgSO₄), the extract was subjected to vacuum-filtration, and then thefiltrated organic solvent was concentrated. The resultant product wasseparated by column chromatography, with the result that desiredintermediate H was obtained with a yield of 57%.

Synthesis of Intermediate I

The intermediate H obtained from the above step, bromoiodobenzene,Pd(PPh₂)₄, and potassium carbonate (K₂CO₃) were dissolved intetrahydrofuran (THF) and a small amount of water, followed by refluxfor 12 hours. Upon completion of the reaction, the reaction product wascooled to room temperature, extracted with dichloromethane (CH₂Cl₂), andwashed with water. A small amount of water was removed from the extractby anhydrous magnesium sulfate (MgSO₄), the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by columnchromatography, with the result that desired intermediate I was obtainedwith a yield of 63%.

Synthesis of Compound 3-14

The intermediate I obtained from the above step,N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, Pd₂(dba)₂, P(tBu)₂,and NaOtBu were dissolved in a toluene solvent, followed by reflux for24 hours at 110° C. Upon completion of the reaction, the reactionproduct was subjected to vacuum filtration through Celite and silica gelby using a hot toluene solvent. The temperature of the filtrate wascooled to room temperature, and then the precipitated product wasrecrystallized again using toluene and acetone, with the result thatdesired compound 3-14 was obtained by a yield of 68%.

4. Synthesis Method of Compound 4-8

With reference to Reaction Scheme 4 above, preparation methods ofintermediates J and K and a preparation method of compound 4-8 will bedescribed below.

Synthesis of Intermediate J

The intermediate G obtained from the above step was dissolved inanhydrous tetrahydrofurane (THF), and the temperature of the reactantswas lowered to −78° C. n-BuLi (2.5 M in hexane) was slowly addeddropwise to the reactants, and then the reactants were stirred for 1hour at 0° C. Subsequently, the temperature of the reactants was loweredto −78° C., and a triisopropyl borate solution dissolved intetrahydrofuran (THF) was added dropwise to the reactants, followed bystirring for 12 hours at room temperature. Upon completion of thereaction, the reaction product was added with 1N—HCl aqueous solution,stirred for 30 minutes, and then extracted with ether. A small amount ofwater was removed from the extract by anhydrous magnesium sulfate(MgSO₄), the extract was subjected to vacuum-filtration, and then thefiltrated organic solvent was concentrated. The resultant product wasseparated by column chromatography, with the result that desiredintermediate J was obtained with a yield of 61%.

Synthesis of Intermediate K

The intermediate J obtained from the above step, bromoiodobenzene,Pd(PPh₃)₄, and potassium carbonate (K₂CO₃) were dissolved intetrahydrofuran (THF) and a small amount of water, followed by refluxfor 12 hours. Upon completion of the reaction, the reaction product wascooled to room temperature, extracted with dichloromethane (CH₂Cl₂), andwashed with water. A small amount of water was removed from the extractby anhydrous magnesium sulfate (MgSO₄), the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by columnchromatography, with the result that desired intermediate K was obtainedwith a yield of 66%.

Synthesis of Compound 4-8

The intermediate K obtained from the above step,N-(biphenyl-4-yl)naphthalene-1-amine, Pd₂(dba)₃, P(tBu)₃, and NaOtBuwere dissolved in a toluene solvent, followed by reflux for 24 hours at110° C. Upon completion of the reaction, the reaction product wassubjected to vacuum filtration through Celite and silica gel by using ahot toluene solvent. The temperature of the filtrate was cooled to roomtemperature, and then the precipitated product was recrystallized againusing toluene and acetone, with the result that desired compound 4-8 wasobtained by a yield of 65%.

5. Synthesis Method of Compound 5-1

With reference to Reaction Scheme 5 above, preparation methods ofintermediate L and compound 5-1 will be described below.

Synthesis of Intermediate L

The intermediate H obtained from the above step, 1,3,5-tribromobenzene,Pd(PPh₃)₄, and potassium carbonate (K₂CO₃) were dissolved intetrahydrofuran (THF) and a small amount of water, followed by refluxfor 12 hours. Upon completion of the reaction, the reaction product wascooled to room temperature, extracted with dichloromethane (CH₂Cl₂), andwashed with water. A small amount of water was removed from the extractby anhydrous magnesium sulfate (MgSO₄), the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by columnchromatography, with the result that desired intermediate K was obtainedwith a yield of 42%.

Synthesis of Compound 5-1

The intermediate L obtained from the above step, diphenylamine,Pd₂(dba)₃, P(tBu)₃, and NaOtBu were dissolved in a toluene solvent,followed by reflux for 24 hours at 110° C. Upon completion of thereaction, the reaction product was subjected to vacuum filtrationthrough Celite and silica gel by using a hot toluene solvent. Thetemperature of the filtrate was cooled to room temperature, and then theprecipitated product was recrystallized again using toluene and acetone,with the result that desired compound 5-1 was obtained by a yield of69%.

6. Synthesis Method of Compound 6-3

With reference to Reaction Scheme 6 above, preparation methods ofintermediate M and compound 6-3 will be described below.

Synthesis of Intermediate M

The intermediate J obtained from the above step, 1,3,5-tribromobenzene,Pd(PPh₃)₄, and potassium carbonate (K₂CO₃) were dissolved intetrahydrofuran (THF) and a small amount of water, followed by refluxfor 12 hours. Upon completion of the reaction, the reaction product wascooled to room temperature, extracted with dichloromethane (CH₂Cl₂), andwashed with water. A small amount of water was removed from the extractby anhydrous magnesium sulfate (MgSO₄), the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by columnchromatography, with the result that desired intermediate M was obtainedwith a yield of 49%.

Synthesis of Compound 6-3

The intermediate M obtained from the above step,N-phenylnaphthalene-1-amine, Pd₂(dba)₂, P(tBu)₃, and NaOtBu weredissolved in a toluene solvent, followed by reflux for 24 hours at 110°C. Upon completion of the reaction, the reaction product was subjectedto vacuum filtration through Celite and silica gel by using a hottoluene solvent. The temperature of the filtrate was cooled to roomtemperature, and then the precipitated product was recrystallized againusing toluene and acetone, with the result that desired compound 6-3 wasobtained by a yield of 68%.

Meanwhile, since there are a wide range of substituents for each of R₁to R₆, X, Ar, Y, and Z of compounds represented by Formula 1, SynthesisExamples of only representative compounds of the compounds representedby Formula 1 have been illustratively described. However, othercompounds represented by Formula 1 than those illustratively describedmay also form a part of this specification.

Fabrication and Evaluation of Organic EL Element

An OLED was fabricated according to a conventional method by using eachof the synthesized compounds 1-15, 2-10, 3-14, 4-8, 5-1, and 6-3 as ahole transport material. Each OLED was fabricated by first forming anITO layer (anode) on a glass substrate and then sequentially depositinga hole injection layer (hole injection layer material: 2-TNATA) with athickness of 600 Å, a hole transport layer (hole transport layermaterial: synthesized compound) with a thickness of 300 Å, a lightemitting layer (doped with 7% of BD-052X: Here, BD-052X was a bluefluorescent dopant and 9,10-di(naphthalene-2-yl)anthracene (AND) wasused as a light emitting host material) with a thickness of 450 Å, anelectron transport layer (electron transport layer material:tris(8-quinolinolato)aluminum (Alq₃)) with a thickness of 250 Å, anelectron injection layer (electron injection later material: LiF) with athickness of 10 Å, and an aluminum cathode with a thickness of 1500 Å.

Comparative Test Example 1

For the purpose of comparison with the synthesized compounds, an OLEDwith the same structure was manufactured using a compound represented byFormula 14 below as a hole transport layer material, instead of theinventive compound.

TABLE 1 hole chroma- transport vol- current luminous ticity layer tagedensity efficiency coordinate material (V) (mA/cm²) (cd/A) (x, y)Example compound 1-15 5.4 13.92 8.7 (0.15, 0.14) 1 Example compound 2-106.1 13.74 8.5 (0.15, 0.15) 2 Example compound 3-14 5.1 14.11 9.0 (0.15,0.15) 3 Example compound 4-8  6.2 14.06 8.7 (0.15, 0.14) 4 Examplecompound 5-1  5.5 13.92 8.8 (0.15, 0.14) 5 Example compound 6-3  6.013.88 8.4 (0.15, 0.15) 6 Compara- ADN 7.1 13.47 7.5 (0.15, 0.15) tiveExample 1

As seen from the results noted in Table 1, an OLED using the inventiveOLED material not only has high efficiency and improved color purity,but can also significantly lower driving voltage. Thus, the inventiveOLED material can significantly improve the luminous efficiency and lifespan of an OLED using the inventive material.

It is obvious that even though the inventive compounds are used in otherorganic material layers of an OLED, for example, an emitting layer, anemission assisting layer, an electron injection layer, an electrontransport layer, and a hole injection layer, in addition to a holetransport layer, the same effects can be obtained.

Since terms “comprising,” “including,” “having”, and the like describedmean that one or more corresponding components may exist unless they arespecifically described to the contrary, it shall be construed that oneor more other components can be included. All of the terminologiescontaining one or more technical or scientific terminologies have thesame meanings that persons skilled in the art understand ordinarilyunless they are defined otherwise. A term ordinarily used like thatdefined by a dictionary shall be construed that it has a meaning equalto that in the context of a related description, and shall not beconstrued in an ideal or excessively formal meaning unless it is clearlydefined in the present specification.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit under 35 U.S.C.§119(a) of Korean Patent Application No. 10-2010-0049325, filed on May26, 2010, which is hereby incorporated by reference for all purposes asif fully set forth herein. Further, this application claims the benefitof priority in other countries than U.S., which are hereby incorporatedby reference herein.

What is claimed is:
 1. A compound represented by Formula below:

wherein R₁, R₂, R₃, R₄, R₅, and R₆ are each independently a hydrogenatom, a halogen atom, a cyano group, an alkoxy group, a thiol group, asubstituted or unsubstituted C1 to C50 alkyl group, a substituted orunsubstituted C1 to C50 alkoxy group, a substituted or unsubstituted C1to C50 alkenyl group, a substituted or unsubstituted C5 to C60 arylenegroup, a substituted or unsubstituted C5 to C60 aryl group, asubstituted or unsubstituted C5 to C60 aryloxy group, a substituted orunsubstituted C1 to C50 alkyl group including at least one of sulfur(S), nitrogen (N), oxygen (O), phosphorous (P), and silicon (Si), asubstituted or unsubstituted C5 to C60 heteroaryl group including atleast one of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) andsilicon (Si), or a substituted or unsubstituted C5 to C60 heteroaryloxygroup including at least one of sulfur (S), nitrogen (N), oxygen (O),phosphorous (P) and silicon (Si); X is sulfur (S), oxygen (O), orsilicon (Si); Ar is a hydrogen atom, a substituted or unsubstituted C1to C50 alkyl group, a substituted or unsubstituted C1 to C50 alkenylgroup, a substituted or unsubstituted C5 to C60 arylene group, asubstituted or unsubstituted C5 to C60 aryl group, a substituted orunsubstituted C5 to C60 aryloxy group, a substituted or unsubstituted C1to C50 alkyl group including at least one of sulfur (S), nitrogen (N),oxygen (O), phosphorous (P), and silicon (Si), a substituted orunsubstituted C5 to C60 heteroaryl group including at least one ofsulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si),or a substituted or unsubstituted C5 to C60 heteroaryloxy groupincluding at least one of sulfur (S), nitrogen (N), oxygen (O),phosphorous (P) and silicon (Si); Y is a substituted or unsubstituted C1to C50 alkyl group, a substituted or unsubstituted C1 to C50 alkenylgroup, a substituted or unsubstituted C5 to C60 arylene group, asubstituted or unsubstituted C5 to C60 aryl group, a substituted orunsubstituted C5 to C60 aryloxy group, a substituted or unsubstituted C1to C50 alkyl group including at least one of sulfur (S), nitrogen (N),oxygen (O), phosphorous (P), and silicon (Si), a substituted orunsubstituted C5 to C60 heteroaryl group including at least one ofsulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si),or a substituted or unsubstituted C5 to C60 heteroaryloxy groupincluding at least one of sulfur (S), nitrogen (N), oxygen (O),phosphorous (P) and silicon (Si); n is 1 or 2; Z is S, NR₇R₈, OR₉,PR₁₀R₁₁ or POR₁₀R₁₁, or SiR₁₂ wherein R₇, R₈, R₉, R₁₀, R₁₁, and R₁₂ areeach independently a substituted or unsubstituted C5 to C60 aryl groupor a substituted or unsubstituted C5 to C60 heteroaryl group includingat least one of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P)and silicon (Si), with the proviso that R₇ and R₈ do not bond to eachother to form a ring structure.
 2. The compound as claimed in claim 1,wherein at least one couple of R₁ and R₂, R₂ and R₃, R₃ and R₄, and R₅and R₆ bond to each other to form a ring structure.
 3. The compound asclaimed in claim 1, wherein the compound is represented by one ofFormulas below:


4. An organic electrical element comprising one or more organic materiallayers comprising the compound as claimed in claim
 1. 5. The organicelectrical element as claimed in claim 4, wherein said one or moreorganic material layers are formed to comprise the compound by a solubleprocess.
 6. The organic electrical element as claimed in claim 4,wherein the organic electrical element comprises an organic lightemitting diode (OLED) having a structure in which a first electrode, theone or more organic material layers, and a second electrode aresequentially laminated.
 7. The organic electrical element as claimed inclaim 6, wherein the one or more organic material layers comprise anyone of a hole injection layer, a hole transport layer, a light emittinglayer, an electron transport layer, an electron injection layer, and acombination thereof.
 8. The organic electrical element as claimed inclaim 6, wherein the organic material layers comprise a hole injectionlayer, and the compound is used as a hole transport material in the holetransport layer.
 9. A terminal comprising a display device, whichcomprises the organic electrical element as claimed in claim 6, and acontrol unit for driving the display device.
 10. The terminal as claimedin claim 9, wherein the organic electrical element comprises any one ofan organic light emitting diode (OLED), an organic solar cell, anorganic photo conductor (OPC) drum, and an organic transistor (organicTFT).